JP4743115B2 - ポジ型感光性樹脂組成物、それを用いたレリーフパターン、及び固体撮像素子 - Google Patents
ポジ型感光性樹脂組成物、それを用いたレリーフパターン、及び固体撮像素子 Download PDFInfo
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- JP4743115B2 JP4743115B2 JP2006510911A JP2006510911A JP4743115B2 JP 4743115 B2 JP4743115 B2 JP 4743115B2 JP 2006510911 A JP2006510911 A JP 2006510911A JP 2006510911 A JP2006510911 A JP 2006510911A JP 4743115 B2 JP4743115 B2 JP 4743115B2
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- Prior art keywords
- resin composition
- photosensitive resin
- carbon atoms
- compound
- positive photosensitive
- Prior art date
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- 239000011342 resin composition Substances 0.000 title claims description 111
- 238000003384 imaging method Methods 0.000 title claims description 5
- -1 quinonediazide compound Chemical class 0.000 claims description 108
- 229920000642 polymer Polymers 0.000 claims description 61
- 150000001875 compounds Chemical class 0.000 claims description 52
- 229920006015 heat resistant resin Polymers 0.000 claims description 46
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 41
- 229920005989 resin Polymers 0.000 claims description 41
- 239000011347 resin Substances 0.000 claims description 41
- 125000000962 organic group Chemical group 0.000 claims description 39
- 239000002245 particle Substances 0.000 claims description 38
- 125000004432 carbon atom Chemical group C* 0.000 claims description 37
- 238000002834 transmittance Methods 0.000 claims description 34
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- 239000000178 monomer Substances 0.000 claims description 24
- 238000010438 heat treatment Methods 0.000 claims description 21
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 239000010954 inorganic particle Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 229920001577 copolymer Polymers 0.000 claims description 8
- 229920003986 novolac Polymers 0.000 claims description 7
- 229920003987 resole Polymers 0.000 claims description 5
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- 229920001519 homopolymer Polymers 0.000 claims description 3
- 230000001678 irradiating effect Effects 0.000 claims description 3
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- 238000005562 fading Methods 0.000 claims 1
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 28
- 230000015572 biosynthetic process Effects 0.000 description 25
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- 238000000034 method Methods 0.000 description 14
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- 125000001931 aliphatic group Chemical group 0.000 description 8
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Natural products C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 8
- LZCLXQDLBQLTDK-UHFFFAOYSA-N ethyl 2-hydroxypropanoate Chemical compound CCOC(=O)C(C)O LZCLXQDLBQLTDK-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 7
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 7
- 150000008065 acid anhydrides Chemical class 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000013256 coordination polymer Substances 0.000 description 7
- 229960000956 coumarin Drugs 0.000 description 7
- 235000001671 coumarin Nutrition 0.000 description 7
- 150000004985 diamines Chemical class 0.000 description 7
- MSTZGVRUOMBULC-UHFFFAOYSA-N 2-amino-4-[2-(3-amino-4-hydroxyphenyl)-1,1,1,3,3,3-hexafluoropropan-2-yl]phenol Chemical compound C1=C(O)C(N)=CC(C(C=2C=C(N)C(O)=CC=2)(C(F)(F)F)C(F)(F)F)=C1 MSTZGVRUOMBULC-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010034972 Photosensitivity reaction Diseases 0.000 description 6
- 239000004642 Polyimide Substances 0.000 description 6
- 125000003545 alkoxy group Chemical group 0.000 description 6
- 230000003197 catalytic effect Effects 0.000 description 6
- 125000001033 ether group Chemical group 0.000 description 6
- 229910052731 fluorine Inorganic materials 0.000 description 6
- 125000001153 fluoro group Chemical group F* 0.000 description 6
- 230000036211 photosensitivity Effects 0.000 description 6
- 229920001721 polyimide Polymers 0.000 description 6
- 238000012545 processing Methods 0.000 description 6
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 5
- HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 5
- SDDLEVPIDBLVHC-UHFFFAOYSA-N Bisphenol Z Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCCC1 SDDLEVPIDBLVHC-UHFFFAOYSA-N 0.000 description 5
- GTDPSWPPOUPBNX-UHFFFAOYSA-N ac1mqpva Chemical compound CC12C(=O)OC(=O)C1(C)C1(C)C2(C)C(=O)OC1=O GTDPSWPPOUPBNX-UHFFFAOYSA-N 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 150000002367 halogens Chemical class 0.000 description 5
- 125000004464 hydroxyphenyl group Chemical group 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 229920005575 poly(amic acid) Polymers 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 5
- 230000035945 sensitivity Effects 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- JESXATFQYMPTNL-UHFFFAOYSA-N 2-ethenylphenol Chemical compound OC1=CC=CC=C1C=C JESXATFQYMPTNL-UHFFFAOYSA-N 0.000 description 4
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
- HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 description 4
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- JHGFRCLDPHKRBS-UHFFFAOYSA-N [Sn+2]=O.[O-2].[Zr+4].[O-2].[O-2] Chemical compound [Sn+2]=O.[O-2].[Zr+4].[O-2].[O-2] JHGFRCLDPHKRBS-UHFFFAOYSA-N 0.000 description 4
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- 238000000576 coating method Methods 0.000 description 4
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- 125000004122 cyclic group Chemical group 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 4
- 229940116333 ethyl lactate Drugs 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 4
- 229910001887 tin oxide Inorganic materials 0.000 description 4
- 229910001928 zirconium oxide Inorganic materials 0.000 description 4
- CFTSORNHIUMCGF-UHFFFAOYSA-N (1,1,1,3,3,3-hexafluoro-2-phenylpropan-2-yl)benzene Chemical group C=1C=CC=CC=1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1 CFTSORNHIUMCGF-UHFFFAOYSA-N 0.000 description 3
- QUWAJPZDCZDTJS-UHFFFAOYSA-N 2-(2-hydroxyphenyl)sulfonylphenol Chemical group OC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1O QUWAJPZDCZDTJS-UHFFFAOYSA-N 0.000 description 3
- QNHYFFOMUQQWPR-UHFFFAOYSA-N 2-[1,1,1,3,3,3-hexafluoro-2-(2-hydroxyphenyl)propan-2-yl]phenol Chemical group OC1=CC=CC=C1C(C(F)(F)F)(C(F)(F)F)C1=CC=CC=C1O QNHYFFOMUQQWPR-UHFFFAOYSA-N 0.000 description 3
- MILSYCKGLDDVLM-UHFFFAOYSA-N 2-phenylpropan-2-ylbenzene Chemical group C=1C=CC=CC=1C(C)(C)C1=CC=CC=C1 MILSYCKGLDDVLM-UHFFFAOYSA-N 0.000 description 3
- GPXCORHXFPYJEH-UHFFFAOYSA-N 3-[[3-aminopropyl(dimethyl)silyl]oxy-dimethylsilyl]propan-1-amine Chemical compound NCCC[Si](C)(C)O[Si](C)(C)CCCN GPXCORHXFPYJEH-UHFFFAOYSA-N 0.000 description 3
- OGRAOKJKVGDSFR-UHFFFAOYSA-N 6-Oxy-pseudocumol Natural products CC1=CC(C)=C(C)C(O)=C1 OGRAOKJKVGDSFR-UHFFFAOYSA-N 0.000 description 3
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- 235000010724 Wisteria floribunda Nutrition 0.000 description 3
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- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 125000006267 biphenyl group Chemical group 0.000 description 3
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- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
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- 238000007865 diluting Methods 0.000 description 3
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- 125000001188 haloalkyl group Chemical group 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 3
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- FMLYSTGQBVZCGN-UHFFFAOYSA-N oxosilicon(2+) oxygen(2-) titanium(4+) Chemical compound [O-2].[Ti+4].[Si+2]=O.[O-2].[O-2] FMLYSTGQBVZCGN-UHFFFAOYSA-N 0.000 description 3
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 3
- 125000006158 tetracarboxylic acid group Chemical group 0.000 description 3
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 3
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- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 2
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- NKTOLZVEWDHZMU-UHFFFAOYSA-N 2,5-xylenol Chemical compound CC1=CC=C(C)C(O)=C1 NKTOLZVEWDHZMU-UHFFFAOYSA-N 0.000 description 2
- NXXYKOUNUYWIHA-UHFFFAOYSA-N 2,6-Dimethylphenol Chemical compound CC1=CC=CC(C)=C1O NXXYKOUNUYWIHA-UHFFFAOYSA-N 0.000 description 2
- LKMJVFRMDSNFRT-UHFFFAOYSA-N 2-(methoxymethyl)oxirane Chemical compound COCC1CO1 LKMJVFRMDSNFRT-UHFFFAOYSA-N 0.000 description 2
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- KZLDGFZCFRXUIB-UHFFFAOYSA-N 2-amino-4-(3-amino-4-hydroxyphenyl)phenol Chemical group C1=C(O)C(N)=CC(C=2C=C(N)C(O)=CC=2)=C1 KZLDGFZCFRXUIB-UHFFFAOYSA-N 0.000 description 2
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- MBGGFXOXUIDRJD-UHFFFAOYSA-N 4-Butoxyphenol Chemical compound CCCCOC1=CC=C(O)C=C1 MBGGFXOXUIDRJD-UHFFFAOYSA-N 0.000 description 2
- HXDOZKJGKXYMEW-UHFFFAOYSA-N 4-ethylphenol Chemical compound CCC1=CC=C(O)C=C1 HXDOZKJGKXYMEW-UHFFFAOYSA-N 0.000 description 2
- JXYITCJMBRETQX-UHFFFAOYSA-N 4-ethynylaniline Chemical compound NC1=CC=C(C#C)C=C1 JXYITCJMBRETQX-UHFFFAOYSA-N 0.000 description 2
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PCT/JP2005/003464 WO2005088396A1 (ja) | 2004-03-12 | 2005-03-02 | ポジ型感光性樹脂組成物、それを用いたレリーフパターン、及び固体撮像素子 |
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JP (1) | JP4743115B2 (zh) |
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CN (1) | CN1930522B (zh) |
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JP2004310076A (ja) * | 2003-03-26 | 2004-11-04 | Sumitomo Bakelite Co Ltd | ポジ型感光性樹脂組成物並びに半導体装置及び表示素子 |
JP2007122024A (ja) * | 2005-09-28 | 2007-05-17 | Toray Ind Inc | 感光性組成物 |
JP5299739B2 (ja) * | 2007-10-15 | 2013-09-25 | 富士電機株式会社 | X線用屈折レンズユニットおよびx線用屈折レンズの製造方法 |
KR101461123B1 (ko) * | 2008-05-08 | 2014-11-14 | 삼성디스플레이 주식회사 | 표시 기판의 제조 방법 및 이를 포함하는 표시 장치의 제조방법 |
KR101113063B1 (ko) * | 2008-05-22 | 2012-02-15 | 주식회사 엘지화학 | 폴리이미드와 노볼락 수지를 포함하는 감광성 수지 조성물 |
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JP5799182B1 (ja) * | 2014-10-03 | 2015-10-21 | 富士フイルム株式会社 | シロキサン樹脂組成物、これを用いた透明硬化物、透明画素、マイクロレンズ、固体撮像素子 |
JPWO2016148176A1 (ja) * | 2015-03-19 | 2017-12-28 | 東レ株式会社 | ポジ型感光性樹脂組成物、硬化膜、tft基板、層間絶縁膜、表示装置、およびその製造方法 |
TW201800860A (zh) * | 2015-12-17 | 2018-01-01 | 陶氏全球科技責任有限公司 | 具有高介電常數之光可成像薄膜 |
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JP6699661B2 (ja) * | 2016-03-28 | 2020-05-27 | 東レ株式会社 | 感光性樹脂成物 |
JP7296746B2 (ja) * | 2019-03-06 | 2023-06-23 | 太陽ホールディングス株式会社 | ポジ型感光性樹脂組成物、ドライフィルム、硬化物、および電子部品 |
US11675266B2 (en) | 2021-04-15 | 2023-06-13 | Industrial Technology Research Institute | Photosensitive compound, photosensitive composition, and patterning method |
CN113485072B (zh) * | 2021-06-22 | 2023-11-07 | 北京科华微电子材料有限公司 | 一种光刻胶组合物及其用途 |
KR20240031210A (ko) * | 2021-07-05 | 2024-03-07 | 가부시끼가이샤 레조낙 | 감광성 수지 조성물, 영구 레지스트, 영구 레지스트의 형성 방법, 및 영구 레지스트용 경화막의 검사 방법 |
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- 2005-03-02 KR KR1020067018518A patent/KR101150593B1/ko active IP Right Grant
- 2005-03-02 US US10/590,366 patent/US20080193718A1/en not_active Abandoned
- 2005-03-02 WO PCT/JP2005/003464 patent/WO2005088396A1/ja not_active Application Discontinuation
- 2005-03-02 JP JP2006510911A patent/JP4743115B2/ja not_active Expired - Fee Related
- 2005-03-02 EP EP05719779.0A patent/EP1724640B1/en not_active Not-in-force
- 2005-03-02 CN CN2005800079347A patent/CN1930522B/zh not_active Expired - Fee Related
- 2005-03-09 TW TW094107131A patent/TWI370325B/zh active
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Also Published As
Publication number | Publication date |
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CN1930522B (zh) | 2013-06-12 |
WO2005088396A1 (ja) | 2005-09-22 |
EP1724640A1 (en) | 2006-11-22 |
TWI370325B (en) | 2012-08-11 |
EP1724640B1 (en) | 2015-11-18 |
US20080193718A1 (en) | 2008-08-14 |
CN1930522A (zh) | 2007-03-14 |
KR20070007095A (ko) | 2007-01-12 |
JPWO2005088396A1 (ja) | 2008-01-31 |
EP1724640A4 (en) | 2010-04-07 |
KR101150593B1 (ko) | 2012-06-01 |
TW200532374A (en) | 2005-10-01 |
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